For casual David Bowie fans who spin the radio hits and not much else, A Clockwork Orange may not be the first work of science fiction that comes to mind when chewing on the well-read singer’s labyrinth of influences from the realms of film, literature, fashion, and avant-garde art. After all, whether we’re referring to Anthony Burgess’ 1962 novel or Stanley Kubrick’s notorious film adaption from 1971, the story is a blend of pitch-black satire, graphic violence, and Cold War-inspired dystopia that feels worlds removed from the cosmic-hippiedom-meets-androgynous-space-alien quirkiness soaked into Bowie’s most popular expressions of sci-fi rock: “Space Oddity,” “Starman,” “Life on Mars?”—even the riff-fueled “Ziggy Stardust.” In fact, a more apt connection might be Kubrick’s other landmark from the same era: 2001: A Space Odyssey. Released in 1968 (just over a year before Apollo 11’s touchdown on the moon ignited a global fascination with space travel), the director’s sweeping meditation on human evolution, outer space, and extraterrestrial life slammed into psychedelic culture like an asteroid, helping to unleash a whole new movement in space rock.

However, dig deeper into Bowie’s cluttered universe (lyrics, interviews, photographs, production credits, etc.), and relics of his fascination with A Clockwork Orange emerge in all corners. It’s a fascination that lasted throughout his career, right up through the release of 2016’s Blackstar, a brilliant, strange, and moodily intoxicating album awash in sci-fi references.

Let’s begin with the singer’s ever-changing visual aesthetic: Bowie himself oncestated to Rolling Stone writer David Sinclair that the look for his 1972 classic The Rise and Fall of Ziggy Stardust and the Spiders from Mars reflected in part his love of the outfits worn by the sociopathic antihero Alex (played by Malcolm McDowell) and his ultraviolent droogs. Those costumes (black bowler hats, bovver boots, suspenders, codpieces) were the brainchild of designer Milena Canonero; by appropriating elements of “London street style,” she helped lay the groundwork for an iconic (and much imitated) look that wound up seeping into glam, punk, hardcore, and even heavy metal. Incidentally, Canonero and Bowie eventually worked together on 1983’s The Hunger, an erotic vampire flick sporting heavy Dario Argento vibes.

Bowie again turned to the film for inspiration during the making of 1973’s Aladdin Sane, a harder-rocking album that finds the singer’s alter-ego turning mischievous, even nasty at times, much like Alex. In addition to sleeve art featuring airbrush work from Philip Castle, whom Kubrick hired to design the movie’s infamously outlandishposters, there were some seriously Clockworkian wardrobe moves, including Bowie’s classicprinted silk turtleneck.

Shifting from aesthetics to the music itself, let’s return to The Rise and Fall of Ziggy Stardust and the Spiders from Mars. While touring in support of the record, Bowie opened concerts with a recording of Beethoven’s Symphony No. 9, yet another nod to Alex, who describes the piece as “bliss and heaven” in one of the movie’s most bitingscenes. There’s also the use of the word “droogie” in “Suffragette City.” Though a fairly minor reference, it speaks volumes about Bowie’s intimate understanding of Burgess’ original vision. After all, “Suffragette City” isn’t one of Ziggy’s orchestral ballads, floating dreamily like an orbiting satellite. It’s gnarly proto-punk inspired by The Velvet Underground and The Stooges—exactly the kind of slasher you’d expect a violent street gang to blast before a night of smashing storefronts and busting heads.

Again, this seems like an odd fit for the red-haired Bowie, who (truth be told) never fully embraced the sneering menace that would come to be associated with punk rock in the late ’70s. But much like The Rolling Stones’ Mick Jagger (who interestingly enough owned the movie rights to the novel for a short while), he certainly flirted with such notions. Bowie seemed attracted to the transgressive darkness that often surrounds youth culture and street gangs, especially as they are portrayed in the book and film incarnations of A Clockwork Orange, both of which, it should be noted, were censored and condemned on numerous occasions in the United Kingdom and the United States. They possessed a undeniable and dangerous allure. Back in the ’70s, any artist who dared make allusions to them clearly was looking to be edgy.

But it was more than just trying to be provocative (though that always was a factor during his glam years). Bowie truly loved A Clockwork Orange, of which his most passionate expression pops up on the previously mentioned Blackstar and the cryptic “Girl Loves Me.” Pay close attention to the lyrics and you’ll notice how the singer, displaying a linguist’s virtuosity, brilliantly litters the song with theNadsat spoken by Alex and the droogs (itself a Nadsat term). Originally conceived by Burgess, it basically is working-class British slang heavily inspired by Russian:

Bowie was a sci-fijunkie, one well-versed in the writings of Michael Moorcock, J.G. Ballard, William S. Burroughs, and George Orwell. He especially loved Orwell’s dystopian landmark Nineteen Eighty-Four, which served as the thematic basis for 1974’s Diamond Dogs. On top of all that, he starred in the cult flick The Man Who Fell to Earth and in 2013 was inducted into the Museum of Pop Culture’s Science Fiction and Fantasy Hall of Fame. But the fact that Bowie returns to A Clockwork Orange on Blackstar, which he knew would be his last album, drives home the work’s stature in his personal universe. Deep down Bowie really was a droog.